‘My girlfriend is a millionaire – and I’m not’

She shops in Prada, he buys his clothes in charity shops. Rob Crossan explains how love works across the financial divide – just don’t tell her about the meal deals

Have you ever seen a female multimillionaire stare blankly at a pork pie? Anna, at the age of 41, had never seen one before her first picnic with me last week. The look on her face as she examined it suggested an inner feeling that a long and sustained run of good fortune in her life had just come to a sad and very sudden end. She carefully handed me the hefty sized pie (which I’d bought from the Fortnum & Mason deli counter earlier that day) unaware of just how much I’d paid for it in order to find a middle ground between her cosmopolitan wealth and my still oft-provincial foodie preferences.

Getting to her feet, she stepped out of the shadow of the tree we had been lounging under in the more fashionable eastern end of Hampstead Heath. ‘I do appreciate the effort, Rob,’ she said kindly. ‘But Soho House has ice buckets and champagne on its roof terrace.’ Clearly my romantic picnic was a bad idea. ‘I should probably never introduce you to pork scratchings,’ I blustered, as we walked to the car park. I chucked the pork pie away and climbed into her Aston Martin, a two-step act that raised me around six social classes in the space of four seconds. I’d never felt more alive, or confused. Such is life when you’re dating a millionaire.

Anna and I met each other on a dating site 18 months ago. It was an ordinary one, not one of those notorious ‘cocaine and comeuppance’ sites for the supposed uber-rich. Not that I would have remotely been considered eligible for inclusion in that upper realm of online dating. Anna’s various companies have a yearly turnover of around £120 million; I earn about £45,000 a year as a freelance writer and radio presenter. She has her sports cars; I have a Tube pass. She drinks champagne; I drink prosecco – often from Aldi. She’s been asked to be a dragon on Dragon’s Den; I’ve been asked to go on BBC Radio Scotland to talk about crisps. We both said ‘no’ to those last respective offers, by the way.

Coming from Russia and fleeing with her family after the fall of the Soviet Union, Anna worked her way up from her first job in the UK as a call-centre worker into a tech entrepreneur, who lives a life of constructing multinational business deals alongside managing a property portfolio stretching from Cape Town to Canada. She does all this while having a social milieu that runs from outings with her personal shopper in Mayfair to first-class flights to New York for holidays with her friends. Petite, blonde and with a penchant for dressing in red, Anna’s success is as much down to her (seemingly effortless) ability to charm people as it is about possessing stone-cold business chutzpah.

Having not seen her cut a deal in the boardroom, I can’t attest to how much she plays hardball at work. But very little of that steel seems to transfer over to her personal life. This is a woman who earlier this year took a recently dumped female friend on a ‘feel good again’, all expenses paid holiday to Thailand; a woman who loves to listen. As I once overheard her say, ‘There’s a direct connection between people who talk about themselves too much and people who won’t be there for you when it counts.’ It’s hardly Shakespeare but, as a caring bromide, it’s pretty good for a former Soviet citizen from the Black Sea.

So, why is Anna interested in a man who grew up on the Wirral, buys books from charity shops and saves money by purchasing lunchtime meal deals? Well, one reason, of course, is that she doesn’t know about the last part of the sentence that you’ve just read. Another is that, despite her not revealing her wealth in her dating profile, I figured having looked at the quality of her clothes in her photos that I should up my game a bit beyond a happy-hour bottle of Sauvignon Blanc in Soho.

I arranged to meet her in a hotel bar in Mayfair for our first date. But, as she would later tell me, ‘I would have gone to Wetherspoons if you’d wanted to.’ Because she admitted on the first night we spent together that she’d spotted something in me beyond the surface of my dating profile before we even met that she’d been seeking for rather a long time. Anna was (fruitlessly) looking for a morally upstanding man of strong values in a dating scene of bankers, property developers and the inherited rich. (Insert your own needles and haystack joke here.) I was, equally fruitlessly, looking for a happy and contented woman in a dating scene awash with bored mature students, frustrated ‘undiscovered’ actors and depressed public-sector apparatchiks, who would tell me they were going to get started on writing their first novel ‘any day now’.

Anna is one of the few people I’ve met while dating in the last few years who isn’t either unhappy with their career or, more commonly, still talking in their early forties about what they’d like to do with their lives. Similarly – and nobody is more surprised by this than me – I am, in Anna’s eyes, one of the few men she’s met of late who has some sort of moral ethical code beyond continual selfish self-reward. What I’ve realised through dating such a rich woman is that the most impressive thing in another person isn’t money at all, it’s success. And these two things don’t necessarily go hand in silk-gloved hand with each other. Let me explain.

Call me impatient, but just having ambition or potential at the age of 40 isn’t enough. There needs to be some ‘achievement’. And by this I don’t mean having coined your first million; I mean you should be certain of what you want in life, and be well on the way to getting it. If you’ve just jacked in your career in banking to retrain as a life coach or a mountain guide, then you’re probably not rich any more. But if doing this (rather than complaining about your current predicament) means you’re a happier person, then not only are you a massive success in a much more important way but you’re also a colossal rarity on the dating scene.

Anna might be rare in having both the money and the happiness, but it’s the success not the salary that really attracts me to her. For somebody with the busiest schedule of any human I know, she gives our relationship an amazing amount of thought and effort. When I’m stuck in south London on deadline while she’s in Miami, I can be sure that I’ll get a text asking how I am. We don’t talk about our jobs that often with each other, and when we do it’s for the other to listen, not to offer advice. We’re most comfortable when we’re lying on the sofa together or at a bar talking about books, box sets, the state of Russia today and (a favourite of Anna’s) why British men can’t ever wear trousers that fit them properly – an area where, she claims, Russian males are world leaders. Despite all this, though, I confess I’m still not quite sure I can be completely myself around her at all times. I go to unnecessary lengths to never accept any gifts from Anna through fear of being labelled a gold digger by any third party – her friends or mine. My continuing blue-collar tastes in deli food and her allergy to any form of public transport makes me wonder if we can ever truly be as comfortable in each other’s worlds as we are in our own. For that to happen, she’ll need a Tube map and I’ll need a new suit at the very, very least.

I’m not a penny richer since I started dating Anna, but it’s taken having such close proximity to money to make me realise just how unimportant it is when it comes to what counts. The problem is that, in the UK more than anywhere else in the First World, the chances of meeting and romancing someone so far removed from your own class or salary bracket hasn’t changed much since the Victorian age. Even in 2017, there’s a part of me that still feels a little like a bearded Eliza Doolittle when I put a tux on to join Anna at a dinner event. Yet she doesn’t want to change me; she just wants me to experience new things. Why do us Brits still seem to feel that doing this is tantamount to some form of collapse of authenticity? Anna has evolved constantly through her life and never felt guilty about it. Yet our British obsession with staying true to our roots, whether they be working, upper or middle, makes us unusually resistant to, and suspicious of, progression or change. It’s why millionaires usually date other millionaires, freelance journalists date account managers and all of us collectively are quite bored. I’m aware that I got lucky. However, my luck hasn’t come from finding someone so rich, but finding somebody so uncorrupted by it and intent on wanting something deeper. Even if she still doesn’t know about my meal-deal habit.